Some complete speculation about the reveals planned for Star Wars for the next couple months, based on the plans for previous projects and my own gut (which could be way off):
End of May/Beginning of June: Vanity Fair cover story about The Rise of Skywalker.
June 8th: World gameplay premiere for Star Wars Jedi: Fallen Order at EA Play, their E3 event.
July 18th-21st: A Star Wars Episode IX: The Rise of Skywalker behind-the-scenes sizzle reel at San Diego Comic Con. Possibly more about The Mandalorian and Clone Wars and maybe some toy reveals for Triple Force Friday.
August 23rd-25th: If there was no Episode IX behind-the-scenes reel at Comic-Con, then it will be shown at Disney's D23 Expo. Otherwise nothing new for The Rise of Skywalker (they might throw a couple of stills to someone like Entertainment Weekly, but nothing major). But maybe the first publically released trailer for The Mandalorian. And possibly the first real hints at the movies from David Benioff/D.B. Weiss and Rian Johnson, including the chance Lucasfilm says who is doing the ones recently announced. We could also get a title for the Cassian Andor series and maybe an announcement of a third series or the release date of Clone Wars. Also, more toy reveals.
October 14th or 21st: The full, theatrical trailer for The Rise of Skywalker debuts at halftime of a Monday Night Football Game. Tickets for the film go on sale immediately after.
End of May/Beginning of June: Vanity Fair cover story about The Rise of Skywalker.
June 8th: World gameplay premiere for Star Wars Jedi: Fallen Order at EA Play, their E3 event.
July 18th-21st: A Star Wars Episode IX: The Rise of Skywalker behind-the-scenes sizzle reel at San Diego Comic Con. Possibly more about The Mandalorian and Clone Wars and maybe some toy reveals for Triple Force Friday.
August 23rd-25th: If there was no Episode IX behind-the-scenes reel at Comic-Con, then it will be shown at Disney's D23 Expo. Otherwise nothing new for The Rise of Skywalker (they might throw a couple of stills to someone like Entertainment Weekly, but nothing major). But maybe the first publically released trailer for The Mandalorian. And possibly the first real hints at the movies from David Benioff/D.B. Weiss and Rian Johnson, including the chance Lucasfilm says who is doing the ones recently announced. We could also get a title for the Cassian Andor series and maybe an announcement of a third series or the release date of Clone Wars. Also, more toy reveals.
October 14th or 21st: The full, theatrical trailer for The Rise of Skywalker debuts at halftime of a Monday Night Football Game. Tickets for the film go on sale immediately after.